Issue 20, 2010
From the journal:

Organic & Biomolecular Chemistry

Synthesis and solid state structure of a hydrazone-disulfidemacrocycle and its dynamic covalent ring-opening under acidic and basic conditions†

Max von Delius,a   Edzard M. Geertsema,a   David A. Leigh*a  and  Alexandra M. Z. Slawinb  

* Corresponding authors

a School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, UK
E-mail: David.Leigh@ed.ac.uk
Fax: +44 131 650 6453
Tel: +44 131 650 4721

b School of Chemistry, University of St. Andrews, Purdie Building, St. Andrews, Fife, UK

Abstract

The synthesis and characterisation, including solid state structure, of a macrocycle containing both a hydrazone and a disulfide linkage is described. Selective ring-opening of the macrocycle under thermodynamic control could be achieved at either the disulfide or the hydrazone linkage by applying mutually exclusive sets of reaction conditions.

Graphical abstract: Synthesis and solid state structure of a hydrazone-disulfide macrocycle and its dynamic covalent ring-opening under acidic and basic conditions

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Article information

DOI
https://doi.org/10.1039/C0OB00214C
Article type
Paper
Submitted
04 Jun 2010
Accepted
08 Jul 2010
First published
20 Aug 2010

Org. Biomol. Chem., 2010,8, 4617-4624

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Synthesis and solid state structure of a hydrazone-disulfide macrocycle and its dynamic covalent ring-opening under acidic and basic conditions

M. von Delius, E. M. Geertsema, D. A. Leigh and A. M. Z. Slawin, Org. Biomol. Chem., 2010, 8, 4617 DOI: 10.1039/C0OB00214C

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